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Identification
NameChlorpromazine
Accession NumberDB00477  (APRD00482)
Typesmall molecule
Groupsapproved
Description

The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class, chlorpromazine’s antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking dopamine receptors. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup. [PubChem]

Structure
Thumb
SynonymsNot Available
Salts
Name/CAS Structure Properties
Chlorpromazine hydrochloride
69-09-0
Thumb
  • InChI Key: FBSMERQALIEGJT-UHFFFAOYSA-N
  • Monoisotopic Mass: 354.072424754
  • Average Mass: 355.325
DBSALT000026
Brand names
NameCompany
ChlorpromanylTechnilab (Canada)
LargactilSpecia
ThorazineGlaxoSmithKline
Brand mixturesNot Available
CategoriesNot Available
CAS number50-53-3
WeightAverage: 318.864
Monoisotopic: 318.095747015
Chemical FormulaC17H19ClN2S
InChI KeyInChIKey=ZPEIMTDSQAKGNT-UHFFFAOYSA-N
InChI
InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3
IUPAC Name
[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine
SMILES
CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2
Mass Specshow(8.36 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzothiazines
SubclassPhenothiazines
Direct parentPhenothiazines
Alternative parentsChlorobenzenes; Aryl Chlorides; Tertiary Amines; Polyamines; Thioethers; Organochlorides
Substituentschlorobenzene; aryl halide; aryl chloride; benzene; tertiary amine; polyamine; thioether; organochloride; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Pharmacology
IndicationFor the treatment of schizophrenia, control nausea and vomiting, For relief of restlessness and apprehension before surgery, adjunct in the treatment of tetanus, control the manifestations of the manic type of manic-depressive illness.
PharmacodynamicsChlorpromazine is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Chlorpromazine has actions at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Chlorpromazine has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
Mechanism of actionChlorpromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Additionally, Chlorpromazine is a weak presynaptic inhibitor of Dopamine reuptake, which may lead to (mild) antidepressive and antiparkinsonian effects. This action could also account for psychomotor agitation and amplification of psychosis (very rarely noted in clinical use).
AbsorptionReadily absorbed from the GI tract. Bioavailability varies due to first-pass metabolism by the liver.
Volume of distribution
  • 20 L/kg
Protein binding> 90% to plasma proteins, primarily albumin
Metabolism

Extensively metabolized in the liver and kidneys. It is extensively metabolized by cytochrome P450 isozymes CYP2D6 (major pathway), CYP1A2 and CYP3A4. Approximately 10 to 12 major metabolite have been identified. Hydroxylation at positions 3 and 7 of the phenothiazine nucleus and the N-dimethylaminopropyl side chain undergoes demethylation and is also metabolized to an N-oxide. In urine, 20% of chlopromazine and its metabolites are excreted unconjugated in the urine as unchanged drug, demonomethylchlorpromazine, dedimethylchlorpromazine, their sulfoxide metabolites, and chlorpromazine-N-oxide. The remaining 80% consists of conjugated metabolites, principally O-glucuronides and small amounts of ethereal sulfates of the mono- and dihydroxy-derivatives of chlorpromazine and their sulfoxide metabolites. The major metabolites are the monoglucuronide of N-dedimethylchlorpromazine and 7-hydroxychlorpromazine. Approximately 37% of the administered dose of chlorpromazine is excreted in urine.

SubstrateEnzymesProduct
Chlorpromazine
hydroxychlorpromazineDetails
Chlorpromazine
    chlorpromazine-N-oxideDetails
    Chlorpromazine
      dedimethylchlorpromazineDetails
      Chlorpromazine
        demonomethylchlorpromazineDetails
        Chlorpromazine
          N-dedimethylchlorpromazineDetails
          Route of eliminationKidneys, ~ 37% excreted in urine
          Half life~ 30 hours
          ClearanceNot Available
          ToxicityAgitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, restlessness
          Affected organisms
          • Humans and other mammals
          PathwaysNot Available
          SNP Mediated EffectsNot Available
          SNP Mediated Adverse Drug ReactionsNot Available
          ADMET
          Predicted ADMET features
          Property Value Probability
          Human Intestinal Absorption + 0.9757
          Blood Brain Barrier + 0.9795
          Caco-2 permeable + 0.8867
          P-glycoprotein substrate Substrate 0.787
          P-glycoprotein inhibitor I Inhibitor 0.7164
          P-glycoprotein inhibitor II Inhibitor 0.8387
          Renal organic cation transporter Inhibitor 0.7557
          CYP450 2C9 substrate Non-substrate 0.7617
          CYP450 2D6 substrate Substrate 0.8919
          CYP450 3A4 substrate Substrate 0.6477
          CYP450 1A2 substrate Inhibitor 0.9305
          CYP450 2C9 substrate Non-inhibitor 0.9071
          CYP450 2D6 substrate Inhibitor 0.9422
          CYP450 2C19 substrate Inhibitor 0.5512
          CYP450 3A4 substrate Non-inhibitor 0.9375
          CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6601
          Ames test Non AMES toxic 0.9133
          Carcinogenicity Non-carcinogens 0.9309
          Biodegradation Not ready biodegradable 1.0
          Rat acute toxicity 3.3196 LD50, mol/kg Not applicable
          hERG inhibition (predictor I) Weak inhibitor 0.9536
          hERG inhibition (predictor II) Inhibitor 0.787
          Pharmacoeconomics
          Manufacturers
          • Glaxosmithkline
          • Actavis mid atlantic llc
          • Pharmaceutical assoc inc div beach products
          • Wockhardt eu operations (swiss) ag
          • Roxane laboratories inc
          • Sandoz inc
          • Abraxis pharmaceutical products
          • Baxter healthcare corp anesthesia and critical care
          • Marsam pharmaceuticals llc
          • Watson laboratories inc
          • Wyeth ayerst laboratories
          • Alpharma us pharmaceuticals division
          • Abbott laboratories pharmaceutical products div
          • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
          • Kv pharmaceutical co
          • Lederle laboratories div american cyanamid co
          • Purepac pharmaceutical co
          • Private formulations inc
          • Usl pharma inc
          • Vangard laboratories inc div midway medical co
          • West ward pharmaceutical corp
          • Parke davis div warner lambert co
          Packagers
          Dosage forms
          FormRouteStrength
          Injection, solutionParenteral25 mg/ml
          SolutionOral10 mg/5 ml
          Solution, concentrateOral100 mg/ml
          Solution, concentrateOral30 mg/ml
          SuppositoryRectal25 mg
          SuppositoryRectal50 mg
          TabletOral10 mg
          TabletOral100 mg
          TabletOral200 mg
          TabletOral25 mg
          TabletOral50 mg
          Prices
          Unit descriptionCostUnit
          Chlorpromazine 25 mg/ml amp8.04USDml
          ChlorproMAZINE HCl 200 mg tablet1.19USDtablet
          Chlorpromazine 200 mg tablet1.05USDtablet
          ChlorproMAZINE HCl 100 mg tablet0.84USDtablet
          ChlorproMAZINE HCl 50 mg tablet0.73USDtablet
          ChlorproMAZINE HCl 25 mg tablet0.55USDtablet
          Chlorpromazine 100 mg tablet0.39USDtablet
          ChlorproMAZINE HCl 10 mg tablet0.37USDtablet
          Chlorpromazine 10 mg tablet0.32USDtablet
          Chlorpromazine 50 mg tablet0.3USDtablet
          Chlorpromazine 25 mg tablet0.17USDtablet
          DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
          PatentsNot Available
          Properties
          Stateliquid
          Experimental Properties
          PropertyValueSource
          melting point177-178Charpentier, P.; U S . Patent 2,645,640; July 14, 1953; assigned to Societe des Usines Chimiques Rhone-Poulenc, France
          boiling point200-205 °C at 8.00E-01 mm HgPhysProp
          water solubility2.55 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
          logP5.41AVDEEF,A (1995)
          logS-5.01ADME Research, USCD
          Caco2 permeability-4.7ADME Research, USCD
          pKa9.3 (at 25 °C)HANSCH,C & LEO,AJ (1985)
          Predicted Properties
          PropertyValueSource
          water solubility4.17e-03 g/lALOGPS
          logP5.18ALOGPS
          logP4.54ChemAxon
          logS-4.9ALOGPS
          pKa (strongest basic)9.2ChemAxon
          physiological charge1ChemAxon
          hydrogen acceptor count2ChemAxon
          hydrogen donor count0ChemAxon
          polar surface area6.48ChemAxon
          rotatable bond count4ChemAxon
          refractivity93.76ChemAxon
          polarizability35.1ChemAxon
          number of rings3ChemAxon
          bioavailability1ChemAxon
          rule of fiveYesChemAxon
          Ghose filterYesChemAxon
          Veber's ruleYesChemAxon
          MDDR-like ruleNoChemAxon
          Spectra
          SpectraNot Available
          References
          Synthesis Reference

          Charpentier, P.; U S . Patent 2,645,640; July 14, 1953; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.

          US2645640
          General Reference
          1. Leucht S, Wahlbeck K, Hamann J, Kissling W: New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. Lancet. 2003 May 10;361(9369):1581-9. Pubmed
          External Links
          ResourceLink
          KEGG DrugD00270
          KEGG CompoundC06906
          PubChem Compound2726
          PubChem Substance46508395
          ChemSpider2625
          ChEBI3647
          ChEMBLCHEMBL71
          Therapeutic Targets DatabaseDAP000374
          PharmGKBPA448964
          IUPHAR83
          Guide to Pharmacology83
          Drug Product Database21342
          RxListhttp://www.rxlist.com/cgi/generic3/chlorpromazine.htm
          Drugs.comhttp://www.drugs.com/cdi/chlorpromazine.html
          PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/chl1441.shtml
          WikipediaChlorpromazine
          ATC CodesNot Available
          AHFS Codes
          • 28:16.08.24
          PDB EntriesNot Available
          FDA labelNot Available
          MSDSshow(75.4 KB)
          Interactions
          Drug Interactions
          Drug
          AmphetamineDecreased anorexic effect, may increase psychotic symptoms
          ArtemetherAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
          BenzphetamineAntipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
          BromocriptineThe phenothiazine decreases the effect of bromocriptine
          CisaprideIncreased risk of cardiotoxicity and arrhythmias
          DexfenfluramineDecreased anorexic effect, may increase psychotic symptoms.
          DextroamphetamineDecreased anorexic effect, may increases psychotic symptoms
          DiethylpropionDecreased anorexic effect, may increase psychotic symptoms
          DihydrocodeinePhenothiazines may enhance hypotensive effects of opioid analgesics. It is recommended to monitor patients for hypotension.
          DonepezilPossible antagonism of action
          FenfluramineDecreased anorexic effect, may increase psychotic symptoms
          GalantaminePossible antagonism of action
          GatifloxacinIncreased risk of cardiotoxicity and arrhythmias
          GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
          GuanethidineChlorpromazine may decrease the effect of guanethidine.
          LevofloxacinIncreased risk of cardiotoxicity and arrhythmias
          LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
          MazindolDecreased anorexic effect, may increase psychotic symptoms
          MesoridazineIncreased risk of cardiotoxicity and arrhythmias
          MethamphetamineDecreased anorexic effect, may increases psychotic symptoms
          MetrizamideIncreased risk of convulsions
          PethidineIncreased sedation and hypotension
          PhendimetrazineDecreased anorexic effect, may increases psychotic symptoms
          PhenmetrazineDecreased anorexic effect, may increase psychotic symptoms
          PhentermineDecreased anorexic effect, may increase psychotic symptoms
          PhenylpropanolamineDecreased anorexic effect, may increase psychotic symptoms
          PindololIncreased effect of both drugs
          PropranololIncreased effect of both drugs
          RivastigminePossible antagonism of action
          SparfloxacinIncreased risk of cardiotoxicity and arrhythmias
          TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor (AChEI), Tacrine, and/or the anticholinergic/antipsychotic, Chlorpromazine, may be reduced due to antagonism. This interaction may be beneficial when the anticholinergic action is a side effect. AChEIs may also augment the central neurotoxic effect of antipsychotics. Monitor for extrapyramidal symptoms and decreased efficacy of both agents.
          TacrolimusAdditive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
          TamoxifenChlorpromazine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
          TamsulosinChlorpromazine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Chlorpromazine is initiated, discontinued, or dose changed.
          TerbinafineTerbinafine may reduce the metabolism and clearance of Chlorpromazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Chlorpromazine if Terbinafine is initiated, discontinued or dose changed.
          TerfenadineIncreased risk of cardiotoxicity and arrhythmias
          TetrabenazineMay cause dopamine deficiency. Similar pharmacologic properties thus combination therapy will worsen the severity of sedative, parkinsonian, and extrapyramidal adverse effects.
          ThioridazineIncreased risk of cardiotoxicity and arrhythmias
          ThiothixeneMay cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
          TolterodineChlorpromazine may decrease the metabolism and clearance of Tolterodine. Monitor for adverse/toxic effects of Tolterodine.
          ToremifeneAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
          TramadolChlorpromazine may decrease the effect of Tramadol by decreasing active metabolite production.
          TrimethobenzamideTrimethobenzamide and Chlorpromazine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
          TrimipramineAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Chlorpromazine, a strong CYP2D6 inhibitor, may also decrease the metabolism and clearance of Trimipramine, a CYP2D6 substrate. Caution should be used during concomitant therapy.
          TriprolidineThe antihistamine, Triprolidine, may increase the arrhythmogenic effect of the phenothiazine, Chlorpromazine. Monitor for symptoms of ventricular arrhythmias. Additive anticholinergic and CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
          TrospiumTrospium and Chlorpromazine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
          VenlafaxineChlorpromazine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Chlorpromazine is initiated, discontinued, or dose changed.
          VorinostatAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
          ZiprasidoneAdditive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy should be avoided.
          ZuclopenthixolAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). Chlorpromazine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if chlorpromazine is initiated, discontinued or dose changed.
          Zuclopenthixol acetateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). Chlorpromazine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if chlorpromazine is initiated, discontinued or dose changed.
          Zuclopenthixol decanoateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). Chlorpromazine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if chlorpromazine is initiated, discontinued or dose changed.
          Food Interactions
          • Avoid alcohol.
          • Take with food to reduce irritation.

          1. D(2) dopamine receptor

          Kind: protein

          Organism: Human

          Pharmacological action: yes

          Actions: antagonist

          Components

          Name UniProt ID Details
          D(2) dopamine receptor P14416 Details

          References:

          1. Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. Pubmed
          2. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. Pubmed
          3. Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. Pubmed
          4. Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. Pubmed
          5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
          6. Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. Pubmed

          2. D(1A) dopamine receptor

          Kind: protein

          Organism: Human

          Pharmacological action: yes

          Actions: antagonist

          Components

          Name UniProt ID Details
          D(1A) dopamine receptor P21728 Details

          References:

          1. Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. Pubmed

          3. 5-hydroxytryptamine receptor 2A

          Kind: protein

          Organism: Human

          Pharmacological action: yes

          Actions: antagonist

          Components

          Name UniProt ID Details
          5-hydroxytryptamine receptor 2A P28223 Details

          References:

          1. Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm. 2000;107(3):295-302. Pubmed
          2. Yamada J, Sugimoto Y, Horisaka K: Serotonin2 (5-HT2) receptor agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) inhibits chlorpromazine- and haloperidol-induced hypothermia in mice. Biol Pharm Bull. 1995 Nov;18(11):1580-3. Pubmed

          4. 5-hydroxytryptamine receptor 1A

          Kind: protein

          Organism: Human

          Pharmacological action: yes

          Actions: antagonist

          Components

          Name UniProt ID Details
          5-hydroxytryptamine receptor 1A P08908 Details

          References:

          1. Cosi C, Koek W: Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT receptors expressed in HeLa cells. Eur J Pharmacol. 2001 Dec 14;433(1):55-62. Pubmed
          2. Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verriele L, Audinot V, Millan MJ: Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study. Eur J Pharmacol. 1998 Aug 21;355(2-3):245-56. Pubmed

          5. Alpha-1A adrenergic receptor

          Kind: protein

          Organism: Human

          Pharmacological action: yes

          Actions: antagonist

          Components

          Name UniProt ID Details
          Alpha-1A adrenergic receptor P35348 Details

          References:

          1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. Pubmed

          6. Alpha-1B adrenergic receptor

          Kind: protein

          Organism: Human

          Pharmacological action: yes

          Actions: antagonist

          Components

          Name UniProt ID Details
          Alpha-1B adrenergic receptor P35368 Details

          References:

          1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. Pubmed

          7. Histamine H1 receptor

          Kind: protein

          Organism: Human

          Pharmacological action: yes

          Actions: antagonist

          Components

          Name UniProt ID Details
          Histamine H1 receptor P35367 Details

          References:

          1. Hals PA, Hall H, Dahl SG: Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12. Pubmed
          2. Church MK, Young KD: The characteristics of inhibition of histamine release from human lung fragments by sodium cromoglycate, salbutamol and chlorpromazine. Br J Pharmacol. 1983 Apr;78(4):671-9. Pubmed
          3. Johnson HG, Miller MD: Inhibition of histamine release and ionophore-induced calcium flux in rat mast cells by lidocaine and chlorpromazine. Agents Actions. 1979 Aug;9(3):239-43. Pubmed
          4. Palmer GC, Wagner HR, Palmer SJ, Manian AA: Histamine-, norepinephrine-, and dopamine-sensitive central adenylate cyclases: effects of chlorpromazine derivatives and butaclamol. Arch Int Pharmacodyn Ther. 1978 Jun;233(2):314-25. Pubmed
          5. Ruffolo RR, Patil PN: Kinetics of blockade of different receptors by chlorpromazine in rabbit stomach strips. Eur J Pharmacol. 1978 Mar 15;48(2):151-7. Pubmed

          1. Cytochrome P450 2D6

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: substrate inhibitor

          Components

          Name UniProt ID Details
          Cytochrome P450 2D6 P10635 Details

          References:

          1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression] Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. Pubmed
          2. Otani K, Aoshima T: Pharmacogenetics of classical and new antipsychotic drugs. Ther Drug Monit. 2000 Feb;22(1):118-21. Pubmed
          3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
          4. Yoshii K, Kobayashi K, Tsumuji M, Tani M, Shimada N, Chiba K: Identification of human cytochrome P450 isoforms involved in the 7-hydroxylation of chlorpromazine by human liver microsomes. Life Sci. 2000;67(2):175-84. Pubmed
          5. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
          6. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

          2. Cytochrome P450 1A2

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: substrate

          Components

          Name UniProt ID Details
          Cytochrome P450 1A2 P05177 Details

          References:

          1. Yoshii K, Kobayashi K, Tsumuji M, Tani M, Shimada N, Chiba K: Identification of human cytochrome P450 isoforms involved in the 7-hydroxylation of chlorpromazine by human liver microsomes. Life Sci. 2000;67(2):175-84. Pubmed
          2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
          3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

          3. Cytochrome P450 3A4

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: substrate

          Components

          Name UniProt ID Details
          Cytochrome P450 3A4 P08684 Details

          References:

          1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
          2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

          4. Cytochrome P450 2E1

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: inhibitor

          Components

          Name UniProt ID Details
          Cytochrome P450 2E1 P05181 Details

          References:

          1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
          2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

          5. Cholinesterase

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: inhibitor

          Components

          Name UniProt ID Details
          Cholinesterase P06276 Details

          References:

          1. Nasello AG, Gidali D, Felicio LF: A comparative study of the anticholinesterase activity of several antipsychotic agents. Pharmacol Biochem Behav. 2003 Jul;75(4):895-901. Pubmed
          2. Muraoka S, Miura T: Inactivation of cholinesterase induced by chlorpromazine cation radicals. Pharmacol Toxicol. 2003 Feb;92(2):100-4. Pubmed
          3. Spinedi A, Pacini L, Limatola C, Luly P, Farias RN: A study of human erythrocyte acetylcholinesterase inhibition by chlorpromazine. Biochem J. 1991 Sep 1;278 ( Pt 2):461-3. Pubmed

          1. Serum albumin

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Components

          Name UniProt ID Details
          Serum albumin P02768 Details

          References:

          1. Kitamura K, Omran AA, Nagata C, Kamijima Y, Tanaka R, Takegami S, Kitade T: Effects of inorganic ions on the binding of triflupromazine and chlorpromazine to bovine serum albumin studied by spectrometric methods. Chem Pharm Bull (Tokyo). 2006 Jul;54(7):972-6. Pubmed
          2. Rukhadze MD, Bezarashvili GS, Sidamonidze NS, Tsagareli SK: Investigation of binding process of chlorpromazine to bovine serum albumin by means of passive and active experiments. Biomed Chromatogr. 2001 Oct;15(6):365-73. Pubmed
          3. Silva D, Cortez CM, Louro SR: Quenching of the intrinsic fluorescence of bovine serum albumin by chlorpromazine and hemin. Braz J Med Biol Res. 2004 Jul;37(7):963-8. Epub 2004 Jun 22. Pubmed

          1. Multidrug resistance protein 1

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: substrate inhibitor

          Components

          Name UniProt ID Details
          Multidrug resistance protein 1 P08183 Details

          References:

          1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed
          2. Boulton DW, DeVane CL, Liston HL, Markowitz JS: In vitro P-glycoprotein affinity for atypical and conventional antipsychotics. Life Sci. 2002 May 31;71(2):163-9. Pubmed

          2. Solute carrier family 22 member 1

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: inhibitor

          Components

          Name UniProt ID Details
          Solute carrier family 22 member 1 O15245 Details

          References:

          1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. Pubmed

          3. Bile salt export pump

          Kind: protein

          Organism: Human

          Pharmacological action: unknown

          Actions: inhibitor

          Components

          Name UniProt ID Details
          Bile salt export pump O95342 Details

          References:

          1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. Pubmed

          Comments
          Drug created on June 13, 2005 07:24 / Updated on April 04, 2014 11:41